N,N',N''-Triphenyl-guanidinium 5-nitro-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-1-ide.

In the title compound, C(19)H(18)N(3) (+.)C(4)H(2)N(3)O(4) (-), the dihedral angles between the phenyl rings and the plane defined by the central guanidinium fragment are in the range 41.3 (1)-66.6 (1)°. The pyrimidine ring of the anion is distorted towards a boat conformation and the nitro group is rotated 11.4 (2)° out of the uracil plane. Hydrogen bonds assemble the ions in infinite helical chains along the b axis.

Related literature

For the non-linear optical properties of 5-nitro­uracil, see: Puccetti et al. (1993 ▶), Youping et al. (1992 ▶). For reports of other triphenyl­guanidine salts, see: Pereira Silva et al. (2006 ▶, 2007a ▶,b ▶), Pereira Silva, Cardoso et al. (2007 ▶). For related literature, see: Allen et al. (1987 ▶); Kemme et al. (1988 ▶); Klement et al. (1995 ▶); Largent et al. (1987 ▶); Pettier & Byrn (1982 ▶); Rao et al. (1995 ▶); Weber et al. (1986 ▶); Zyss et al. (1993 ▶).

Experimental

Crystal data

C19H18N3 +·C4H2N3O4 −

M = 444.45

Monoclinic,

a = 10.7495 (4) Å

b = 15.6892 (7) Å

c = 15.5624 (7) Å

β = 123.456 (3)°

V = 2189.74 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.34 × 0.20 × 0.12 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.822, T max = 0.989

47807 measured reflections

5534 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 0.99

5534 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014244/bt2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014244/bt2707Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H18N3+·C4H2N3O4–	F000 = 928
Mr = 444.45	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5110 reflections
a = 10.7495 (4) Å	θ = 2.3–21.6º
b = 15.6892 (7) Å	µ = 0.10 mm−1
c = 15.5624 (7) Å	T = 293 (2) K
β = 123.456 (3)º	Block, yellow
V = 2189.74 (18) Å3	0.34 × 0.20 × 0.12 mm
Z = 4

Bruker APEX2 CCD area-detector diffractometer	5534 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.086
T = 293(2) K	θmax = 28.6º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.822, Tmax = 0.989	k = −20→21
47807 measured reflections	l = −20→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.1061P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.154	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.22 e Å−3
5534 reflections	Δρmin = −0.17 e Å−3
299 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (11)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.82985 (16)	−0.17695 (11)	0.60642 (13)	0.0729 (5)
O4	0.61600 (16)	0.07278 (11)	0.59408 (15)	0.0968 (6)
O7	0.7653 (2)	0.21285 (11)	0.59093 (15)	0.0949 (6)
O8	0.9257 (2)	0.19450 (12)	0.55194 (16)	0.0940 (6)
N1	0.93683 (17)	−0.06007 (12)	0.58600 (13)	0.0581 (5)
N3	0.72353 (18)	−0.04940 (13)	0.59167 (16)	0.0759 (6)
H3	0.6532	−0.0761	0.5911	0.091*
N5	0.8406 (2)	0.16564 (13)	0.57455 (13)	0.0658 (5)
C2	0.8316 (2)	−0.09943 (17)	0.59504 (16)	0.0596 (6)
C4	0.7147 (2)	0.03782 (16)	0.58914 (17)	0.0668 (6)
C5	0.8282 (2)	0.07584 (14)	0.57999 (14)	0.0555 (5)
C6	0.9311 (2)	0.02398 (15)	0.57896 (15)	0.0585 (6)
H6	1.0030	0.0506	0.5727	0.070*
N6	0.93433 (16)	0.28871 (10)	0.33661 (12)	0.0538 (4)
H6A	1.0086	0.2545	0.3590	0.065*
N7	0.79767 (16)	0.16933 (10)	0.31325 (12)	0.0503 (4)
H7	0.8742	0.1468	0.3667	0.060*
N8	0.67626 (16)	0.29829 (10)	0.24472 (12)	0.0491 (4)
H8	0.6759	0.3411	0.2101	0.059*
C7	0.80155 (19)	0.25245 (12)	0.29824 (14)	0.0464 (5)
C8	0.9677 (2)	0.37724 (13)	0.34492 (14)	0.0539 (5)
C9	0.8938 (3)	0.43773 (15)	0.3642 (2)	0.0768 (7)
H9	0.8184	0.4218	0.3732	0.092*
C10	0.9323 (4)	0.52263 (18)	0.3700 (2)	0.1001 (10)
H10	0.8806	0.5639	0.3811	0.120*
C11	1.0463 (4)	0.5467 (2)	0.3594 (2)	0.1051 (12)
H11	1.0718	0.6038	0.3632	0.126*
C12	1.1207 (3)	0.4857 (2)	0.3434 (2)	0.0959 (10)
H12	1.1990	0.5015	0.3374	0.115*
C13	1.0833 (2)	0.40133 (17)	0.33588 (16)	0.0702 (7)
H13	1.1356	0.3605	0.3247	0.084*
C14	0.67503 (19)	0.11513 (11)	0.24655 (15)	0.0468 (5)
C15	0.6368 (3)	0.05200 (14)	0.28837 (19)	0.0765 (7)
H15	0.6896	0.0452	0.3594	0.092*
C16	0.5197 (4)	−0.00143 (18)	0.2246 (2)	0.1072 (11)
H16	0.4934	−0.0446	0.2526	0.129*
C17	0.4422 (3)	0.00873 (17)	0.1204 (2)	0.0877 (8)
H17	0.3628	−0.0273	0.0776	0.105*
C18	0.4805 (2)	0.07121 (15)	0.07889 (18)	0.0666 (6)
H18	0.4269	0.0781	0.0078	0.080*
C19	0.5977 (2)	0.12417 (13)	0.14139 (15)	0.0535 (5)
H19	0.6250	0.1662	0.1127	0.064*
C20	0.54307 (19)	0.28099 (11)	0.24114 (14)	0.0459 (5)
C21	0.5506 (2)	0.26333 (14)	0.33038 (16)	0.0584 (5)
H21	0.6423	0.2616	0.3931	0.070*
C22	0.4205 (3)	0.24817 (15)	0.3260 (2)	0.0725 (6)
H22	0.4244	0.2356	0.3858	0.087*
C23	0.2860 (3)	0.25168 (17)	0.2335 (2)	0.0795 (7)
H23	0.1988	0.2411	0.2308	0.095*
C24	0.2785 (2)	0.27057 (17)	0.1450 (2)	0.0760 (7)
H24	0.1864	0.2735	0.0826	0.091*
C25	0.4079 (2)	0.28527 (14)	0.14842 (16)	0.0605 (6)
H25	0.4035	0.2980	0.0884	0.073*

	U11	U22	U33	U12	U13	U23
O2	0.0549 (9)	0.0732 (11)	0.0938 (12)	0.0013 (8)	0.0430 (8)	−0.0117 (9)
O4	0.0486 (9)	0.0987 (13)	0.1444 (16)	−0.0064 (8)	0.0541 (10)	−0.0593 (12)
O7	0.1289 (16)	0.0814 (12)	0.1126 (14)	0.0391 (11)	0.0908 (13)	0.0146 (10)
O8	0.0851 (12)	0.0926 (14)	0.1211 (15)	0.0113 (10)	0.0675 (12)	0.0081 (11)
N1	0.0447 (9)	0.0748 (13)	0.0567 (10)	0.0156 (8)	0.0290 (8)	0.0017 (9)
N3	0.0438 (9)	0.0791 (14)	0.1104 (16)	−0.0068 (9)	0.0462 (10)	−0.0360 (11)
N5	0.0622 (11)	0.0797 (14)	0.0520 (11)	0.0232 (10)	0.0293 (9)	0.0050 (9)
C2	0.0385 (10)	0.0779 (16)	0.0564 (13)	0.0058 (10)	0.0224 (9)	−0.0146 (12)
C4	0.0348 (10)	0.0810 (17)	0.0710 (14)	0.0039 (10)	0.0206 (10)	−0.0295 (12)
C5	0.0441 (10)	0.0706 (15)	0.0443 (11)	0.0153 (10)	0.0196 (9)	−0.0054 (10)
C6	0.0468 (11)	0.0790 (16)	0.0500 (12)	0.0149 (10)	0.0270 (9)	0.0049 (11)
N6	0.0370 (8)	0.0558 (10)	0.0650 (10)	−0.0021 (7)	0.0260 (8)	−0.0019 (8)
N7	0.0370 (8)	0.0462 (9)	0.0559 (10)	0.0036 (7)	0.0182 (7)	0.0055 (7)
N8	0.0393 (8)	0.0468 (9)	0.0625 (10)	0.0031 (7)	0.0289 (7)	0.0130 (8)
C7	0.0377 (10)	0.0504 (12)	0.0524 (11)	−0.0005 (8)	0.0257 (8)	0.0006 (9)
C8	0.0458 (10)	0.0578 (13)	0.0475 (11)	−0.0093 (9)	0.0191 (9)	−0.0011 (9)
C9	0.0752 (15)	0.0629 (16)	0.0913 (18)	−0.0108 (12)	0.0452 (14)	−0.0139 (13)
C10	0.104 (2)	0.0608 (17)	0.101 (2)	−0.0072 (16)	0.0347 (18)	−0.0097 (15)
C11	0.105 (2)	0.070 (2)	0.0763 (19)	−0.0331 (18)	0.0098 (17)	0.0112 (15)
C12	0.0807 (19)	0.105 (2)	0.0703 (18)	−0.0443 (18)	0.0218 (15)	0.0132 (16)
C13	0.0525 (12)	0.0899 (18)	0.0590 (13)	−0.0203 (12)	0.0249 (10)	0.0025 (12)
C14	0.0392 (9)	0.0431 (11)	0.0566 (12)	0.0040 (8)	0.0256 (9)	0.0000 (9)
C15	0.0956 (18)	0.0578 (14)	0.0655 (15)	−0.0198 (13)	0.0378 (13)	0.0029 (11)
C16	0.137 (3)	0.081 (2)	0.092 (2)	−0.0555 (19)	0.057 (2)	−0.0047 (16)
C17	0.0882 (18)	0.0767 (18)	0.088 (2)	−0.0355 (14)	0.0420 (16)	−0.0208 (14)
C18	0.0613 (13)	0.0670 (15)	0.0630 (14)	−0.0035 (11)	0.0288 (11)	−0.0089 (11)
C19	0.0505 (11)	0.0527 (12)	0.0600 (13)	0.0007 (9)	0.0321 (10)	0.0009 (10)
C20	0.0417 (10)	0.0421 (11)	0.0577 (12)	0.0052 (8)	0.0299 (9)	0.0059 (9)
C21	0.0543 (12)	0.0613 (13)	0.0646 (13)	0.0073 (10)	0.0359 (11)	0.0101 (10)
C22	0.0781 (16)	0.0782 (16)	0.0897 (17)	0.0069 (13)	0.0643 (15)	0.0110 (13)
C23	0.0579 (14)	0.0906 (18)	0.112 (2)	−0.0022 (12)	0.0608 (16)	−0.0005 (15)
C24	0.0425 (11)	0.1013 (19)	0.0818 (17)	0.0049 (11)	0.0329 (11)	−0.0025 (14)
C25	0.0440 (11)	0.0753 (15)	0.0620 (13)	0.0082 (10)	0.0291 (10)	0.0074 (11)

O2—C2	1.231 (3)	C11—C12	1.356 (4)
O4—C4	1.234 (2)	C11—H11	0.9300
O7—N5	1.224 (2)	C12—C13	1.369 (4)
O8—N5	1.233 (2)	C12—H12	0.9300
N1—C6	1.322 (3)	C13—H13	0.9300
N1—C2	1.362 (3)	C14—C15	1.367 (3)
N3—C4	1.371 (3)	C14—C19	1.375 (3)
N3—C2	1.379 (3)	C15—C16	1.376 (3)
N3—H3	0.8600	C15—H15	0.9300
N5—C5	1.422 (3)	C16—C17	1.364 (4)
C4—C5	1.434 (3)	C16—H16	0.9300
C5—C6	1.380 (3)	C17—C18	1.356 (3)
C6—H6	0.9300	C17—H17	0.9300
N6—C7	1.333 (2)	C18—C19	1.368 (3)
N6—C8	1.422 (2)	C18—H18	0.9300
N6—H6A	0.8600	C19—H19	0.9300
N7—C7	1.330 (2)	C20—C25	1.373 (3)
N7—C14	1.425 (2)	C20—C21	1.374 (3)
N7—H7	0.8600	C21—C22	1.383 (3)
N8—C7	1.337 (2)	C21—H21	0.9300
N8—C20	1.428 (2)	C22—C23	1.368 (3)
N8—H8	0.8600	C22—H22	0.9300
C8—C9	1.373 (3)	C23—C24	1.367 (3)
C8—C13	1.378 (3)	C23—H23	0.9300
C9—C10	1.383 (4)	C24—C25	1.382 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.375 (5)	C25—H25	0.9300
C10—H10	0.9300
C6—N1—C2	117.20 (18)	C11—C12—C13	121.5 (3)
C4—N3—C2	127.8 (2)	C11—C12—H12	119.2
C4—N3—H3	116.1	C13—C12—H12	119.2
C2—N3—H3	116.1	C12—C13—C8	119.7 (3)
O7—N5—O8	121.2 (2)	C12—C13—H13	120.2
O7—N5—C5	119.5 (2)	C8—C13—H13	120.2
O8—N5—C5	119.33 (18)	C15—C14—C19	119.88 (18)
O2—C2—N1	122.85 (19)	C15—C14—N7	119.08 (18)
O2—C2—N3	119.2 (2)	C19—C14—N7	121.02 (17)
N1—C2—N3	117.9 (2)	C14—C15—C16	119.6 (2)
O4—C4—N3	119.4 (2)	C14—C15—H15	120.2
O4—C4—C5	129.0 (2)	C16—C15—H15	120.2
N3—C4—C5	111.65 (18)	C17—C16—C15	120.2 (2)
C6—C5—N5	118.7 (2)	C17—C16—H16	119.9
C6—C5—C4	119.1 (2)	C15—C16—H16	119.9
N5—C5—C4	122.10 (18)	C18—C17—C16	120.2 (2)
N1—C6—C5	126.0 (2)	C18—C17—H17	119.9
N1—C6—H6	117.0	C16—C17—H17	119.9
C5—C6—H6	117.0	C17—C18—C19	120.2 (2)
C7—N6—C8	127.70 (17)	C17—C18—H18	119.9
C7—N6—H6A	116.1	C19—C18—H18	119.9
C8—N6—H6A	116.1	C18—C19—C14	120.0 (2)
C7—N7—C14	124.30 (15)	C18—C19—H19	120.0
C7—N7—H7	117.8	C14—C19—H19	120.0
C14—N7—H7	117.8	C25—C20—C21	120.68 (18)
C7—N8—C20	124.48 (15)	C25—C20—N8	119.28 (18)
C7—N8—H8	117.8	C21—C20—N8	119.99 (17)
C20—N8—H8	117.8	C20—C21—C22	119.4 (2)
N7—C7—N6	118.00 (16)	C20—C21—H21	120.3
N7—C7—N8	121.24 (16)	C22—C21—H21	120.3
N6—C7—N8	120.75 (17)	C23—C22—C21	119.9 (2)
C9—C8—C13	119.7 (2)	C23—C22—H22	120.1
C9—C8—N6	123.18 (19)	C21—C22—H22	120.1
C13—C8—N6	117.1 (2)	C24—C23—C22	120.7 (2)
C8—C9—C10	119.4 (3)	C24—C23—H23	119.7
C8—C9—H9	120.3	C22—C23—H23	119.7
C10—C9—H9	120.3	C23—C24—C25	119.9 (2)
C11—C10—C9	120.7 (3)	C23—C24—H24	120.0
C11—C10—H10	119.6	C25—C24—H24	120.0
C9—C10—H10	119.6	C20—C25—C24	119.5 (2)
C12—C11—C10	118.9 (3)	C20—C25—H25	120.3
C12—C11—H11	120.5	C24—C25—H25	120.3
C10—C11—H11	120.5
C6—N1—C2—O2	−176.90 (19)	C8—C9—C10—C11	−1.8 (4)
C6—N1—C2—N3	2.8 (3)	C9—C10—C11—C12	−0.1 (4)
C4—N3—C2—O2	173.4 (2)	C10—C11—C12—C13	1.1 (4)
C4—N3—C2—N1	−6.2 (3)	C11—C12—C13—C8	−0.2 (4)
C2—N3—C4—O4	−174.6 (2)	C9—C8—C13—C12	−1.7 (3)
C2—N3—C4—C5	5.8 (3)	N6—C8—C13—C12	−179.87 (19)
O7—N5—C5—C6	−169.02 (19)	C7—N7—C14—C15	−141.8 (2)
O8—N5—C5—C6	12.0 (3)	C7—N7—C14—C19	39.8 (3)
O7—N5—C5—C4	9.4 (3)	C19—C14—C15—C16	−0.8 (4)
O8—N5—C5—C4	−169.6 (2)	N7—C14—C15—C16	−179.2 (2)
O4—C4—C5—C6	178.0 (2)	C14—C15—C16—C17	−0.2 (5)
N3—C4—C5—C6	−2.4 (3)	C15—C16—C17—C18	0.4 (5)
O4—C4—C5—N5	−0.4 (3)	C16—C17—C18—C19	0.3 (4)
N3—C4—C5—N5	179.21 (18)	C17—C18—C19—C14	−1.3 (3)
C2—N1—C6—C5	0.1 (3)	C15—C14—C19—C18	1.5 (3)
N5—C5—C6—N1	178.24 (18)	N7—C14—C19—C18	179.85 (18)
C4—C5—C6—N1	−0.2 (3)	C7—N8—C20—C25	−136.65 (19)
C14—N7—C7—N6	−152.77 (18)	C7—N8—C20—C21	45.7 (3)
C14—N7—C7—N8	26.0 (3)	C25—C20—C21—C22	1.2 (3)
C8—N6—C7—N7	−168.86 (18)	N8—C20—C21—C22	178.88 (19)
C8—N6—C7—N8	12.4 (3)	C20—C21—C22—C23	−0.6 (4)
C20—N8—C7—N7	31.5 (3)	C21—C22—C23—C24	−0.4 (4)
C20—N8—C7—N6	−149.75 (18)	C22—C23—C24—C25	0.8 (4)
C7—N6—C8—C9	34.2 (3)	C21—C20—C25—C24	−0.8 (3)
C7—N6—C8—C13	−147.7 (2)	N8—C20—C25—C24	−178.5 (2)
C13—C8—C9—C10	2.7 (3)	C23—C24—C25—C20	−0.2 (4)
N6—C8—C9—C10	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O2i	0.86	1.94	2.794 (2)	174
N7—H7···N1i	0.86	2.21	2.934 (2)	142
N8—H8···O4ii	0.86	2.05	2.887 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O2i	0.86	1.94	2.794 (2)	174
N7—H7⋯N1i	0.86	2.21	2.934 (2)	142
N8—H8⋯O4ii	0.86	2.05	2.887 (2)	163

Symmetry codes: (i) ; (ii) .